Discovery of 3-(1-Amino-2-phenoxyethylidene)-6-methyl-2H-pyran-2,4(3H)-dione Derivatives as Novel Herbicidal Leads
نویسندگان
چکیده
Natural products are one of the resources for discovering novel pesticide leads. Here, by molecular hybridization between natural enamino diketone skeleton and reported herbicide lead compound I, a series 3-(1-aminoethylidene)-6-methyl-2H-pyran-2,4(3H)-dione derivatives (APD) were rationally designed, synthesized tested herbicidal activity in greenhouse. The bioassay results showed that most target compounds possessed good under pre-emergence conditions, which analog APD-II-15 displayed pre-emergent against Abutilon theophrasti Medicus, Amaranthus retroflexus L., Echinochloa crus-galli, Eragrostis curvula (Schrad.) Nees, Avena fatua Cyperus difformis Chenopodium album Ixeris denticulata, Plantago asiatica Capsella bursa-pastoris (Linn.) Medic Flaveria bidentis (L.) Kuntze with > 60% inhibition even at dosage 187.5 g ha−1, crop safety wheat, soybean, millet sorghum 375 ha−1. preliminary study mode action RNA sequencing suggested growth weeds might result from disruptions carbon metabolism formation cytoskeleton. present work indicated be used as further optimization.
منابع مشابه
Crystal structure of 3-{1-[(1-allyl-1H-indazol-6-yl)amino]ethylidene}-6-methyl-2H-pyran-2,4(3H)-dione
In the title compound, C18H17N3O3, the dihedral angle between the planes of the indazole ring system [maximum deviation = 0.012 (1) Å] and the pyran-2,4-dione ring is 54.03 (6)°. An intra-molecular N-H⋯O hydrogen bond closes an S(6) ring. The same H atom also participates in an inter-molecular N-H⋯O hydrogen bond, which generates an inversion dimer. The dimers are linked by weak C-H⋯O contacts,...
متن کامل4-Hydroxy-3-[(4-hydroxy-6-methyl-2-oxo-3,6-dihydro-2H-pyran-3-yl)(3-thienyl)methyl]-6-methyl-3,6-dihydro-2H-pyran-2-one
The asymmetric unit of the title compound, C(17)H(14)O(6)S, contains four crystallographically independent mol-ecules in which the pyran-one units are essentially planar, with maximum deviations of 0.016 (2), 0.019 (2), 0.025 (2), 0.014 (2), 0.020 (2), 0.010 (2), 0.003 (2) and 0.012 (2) Å. One of the thio-phene rings is disordered over two positions, with an occupancy ratio of 0.739 (4):0.261 (...
متن کامل6-Hydroxy-1,2,4-triazine-3,5(2H,4H)-dione Derivatives as Novel d-Amino Acid Oxidase Inhibitors
A series of 2-substituted 6-hydroxy-1,2,4-triazine-3,5(2H,4H)-dione derivatives were synthesized as inhibitors of D-amino acid oxidase (DAAO). Many compounds in this series were found to be potent DAAO inhibitors, with IC50 values in the double-digit nanomolar range. The 6-hydroxy-1,2,4-triazine-3,5(2H,4H)-dione pharmacophore appears metabolically resistant to O-glucuronidation unlike other str...
متن کاملZwitterionic 6-methyl-2-oxo-3-[1-(ureidoiminio)ethyl]-2H-pyran-4-olate monohydrate
The title compound, C(9)H(11)N(3)O(4)·H(2)O, was prepared by the reaction of dehydro-acetic acid and semicarbazide hydro-chloride. It crystallizes in a zwitterionic form with cationic iminium and anionic enolate groups. In the crystal structure, the almost planar mol-ecules are held together by N-H⋯O, O-H⋯O and C-H⋯O hydrogen bonds, some of them involving the water molecules.
متن کامل4-Hydroxy-6-methyl-3-[3-(thiophen-2-yl)acryloyl]-2H-pyran-2-one
The title compound, C13H10O4S, crystallizes with two mol-ecules in the asymmetric unit in which the rings make dihedral angles of 3.9 (1) and 6.0 (1)°; this planarity is due in part to the presence of an intra-molecular O-H⋯O hydrogen bond, which generates an S(6) ring in each mol-ecule. Both mol-ecules represent E isomers with respect to the central C=C bond. In the crystal, mol-ecules are lin...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
ژورنال
عنوان ژورنال: Agronomy
سال: 2023
ISSN: ['2156-3276', '0065-4663']
DOI: https://doi.org/10.3390/agronomy13010202